1-(But-3-yn-1-yl)piperidine → (2-Methoxy-ethyl)-[6-(4-piperidin-1-yl-but-1-ynyl)-pyridin-2-ylmethyl]-amine
Reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][NH:9][CH2:10][CH2:11][O:12][CH3:13])[CH:5]=[CH:4][CH:3]=1.[CH2:14]([N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:15][C:16]#[CH:17]>>[CH3:13][O:12][CH2:11][CH2:10][NH:9][CH2:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([C:17]#[C:16][CH2:15][CH2:14][N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[N:7]=1Participants
3
Procedure
The title compound (13%) was prepared in a manner similar to that described in Example 18, Step D, using (6-bromo-pyridin-2-ylmethyl)-(2-methoxy-ethyl)-amine (0.300 g, 1.23 mmol) and 1-but-3-ynyl-piperidine (0.336 g, 2.45 mmol). MS (ESI): exact mass calcd. for C18H27N3O, 301.44; m/z found, 302.4 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.56 (t, 7.7, 1H), 7.26 (d, J=7.1, 1H), 7.23 (d, J=7.7, 1H), 3.90 (s, 2H), 3.52-3.45 (m, 2H), 3.34 (s, 3H), 2.80 J=5.2, 2H), 2.70-2.59 (m, 4H), 2.48-2.40 (m, 4H), 1.67-1.54 (m, 5H), 1.46-1.38 (m, 2H).
Sources & evidence
- ORD record
- ord-b612647b2bfc4aacbb89a124504454bd
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07423147B2
Reaction notes
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